Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1667-1676.DOI: 10.6023/cjoc202201010 Previous Articles Next Articles
ARTICLES
黄志友a,*(), 李哲陟a, 何波b, 李文胜c, 杨平a, 陈立军a
收稿日期:
2022-01-10
修回日期:
2022-02-12
发布日期:
2022-03-21
通讯作者:
黄志友
基金资助:
Zhiyou Huanga(), Zhezhi Lia, Bo Heb, Wensheng Lic, Ping Yanga, Lijun Chena
Received:
2022-01-10
Revised:
2022-02-12
Published:
2022-03-21
Contact:
Zhiyou Huang
Supported by:
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Zhiyou Huang, Zhezhi Li, Bo He, Wensheng Li, Ping Yang, Lijun Chen. Efficient Ultrasound-Assisted Approach to N-Benzensulfonyl Phenylacetamide via CuSO4/NaAsc Catalysis in Water and Its Inhibition Activity of Seed Germination[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1667-1676.
Entry | Catalyst | Solvent | t/min | Yield/% |
---|---|---|---|---|
1 | CuSO4 (0.1 equiv.)/NaAsc (1.0 equiv.) | tBuOH∶H2O (V∶V=3∶1) | 60 | 63 |
2 | CuSO4 (0.1 equiv.)/NaAsc (1.0 equiv.) | tBuOH∶H2O (V∶V=2∶1) | 60 | 67 |
3 | CuSO4 (0.1 equiv.)/NaAsc (1.0 equiv.) | tBuOH∶H2O (V∶V=1∶2) | 60 | 71 |
4 | CuSO4 (0.1 equiv.)/NaAsc (1.0 equiv.) | H2O | 60 | 83 |
5 | CuSO4 (0.1 equiv.)/NaAsc (0.5 equiv.) | H2O | 60 | 83 |
6 | CuSO4 (0.1 equiv.)/NaAsc (0.4 equiv.) | H2O | 60 | 83 |
7 | CuSO4 (0.1 equiv.)/NaAsc (0.3 equiv.) | H2O | 60 | 78 |
8 | CuSO4 (0.1 equiv.)/NaAsc (0.1 equiv.) | H2O | 60 | 46 |
9 | CuSO4 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 60 | 83 |
10 | CuSO4 (0.02 equiv.)/NaAsc (0.4 equiv.) | H2O | 60 | 71 |
11b | CuSO4 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 95 |
12b | CuSO4•5H2O (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 95 |
13b | Cu(OAc)2•H2O (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 93 |
14b | Cu(OAc)2 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 93 |
15b | CuS (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | < 5 |
16b | CuI (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 45 |
17b | Cu(CF3SO3)2 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 91 |
18b,c | CuSO4 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 13 | 95 |
19b,d | CuSO4 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 6 | 95 |
Entry | Catalyst | Solvent | t/min | Yield/% |
---|---|---|---|---|
1 | CuSO4 (0.1 equiv.)/NaAsc (1.0 equiv.) | tBuOH∶H2O (V∶V=3∶1) | 60 | 63 |
2 | CuSO4 (0.1 equiv.)/NaAsc (1.0 equiv.) | tBuOH∶H2O (V∶V=2∶1) | 60 | 67 |
3 | CuSO4 (0.1 equiv.)/NaAsc (1.0 equiv.) | tBuOH∶H2O (V∶V=1∶2) | 60 | 71 |
4 | CuSO4 (0.1 equiv.)/NaAsc (1.0 equiv.) | H2O | 60 | 83 |
5 | CuSO4 (0.1 equiv.)/NaAsc (0.5 equiv.) | H2O | 60 | 83 |
6 | CuSO4 (0.1 equiv.)/NaAsc (0.4 equiv.) | H2O | 60 | 83 |
7 | CuSO4 (0.1 equiv.)/NaAsc (0.3 equiv.) | H2O | 60 | 78 |
8 | CuSO4 (0.1 equiv.)/NaAsc (0.1 equiv.) | H2O | 60 | 46 |
9 | CuSO4 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 60 | 83 |
10 | CuSO4 (0.02 equiv.)/NaAsc (0.4 equiv.) | H2O | 60 | 71 |
11b | CuSO4 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 95 |
12b | CuSO4•5H2O (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 95 |
13b | Cu(OAc)2•H2O (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 93 |
14b | Cu(OAc)2 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 93 |
15b | CuS (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | < 5 |
16b | CuI (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 45 |
17b | Cu(CF3SO3)2 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 20 | 91 |
18b,c | CuSO4 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 13 | 95 |
19b,d | CuSO4 (0.05 equiv.)/NaAsc (0.4 equiv.) | H2O | 6 | 95 |
Entry | R1 | R2 | 3 | Yield/% | Entry | R1 | R2 | 3 | Yield/% |
---|---|---|---|---|---|---|---|---|---|
1 | 4-CH3 | H | 3a | 95 | 16 | H | 4-CH3 | 3aa | 95 |
2 | 4-CH3 | 4-F | 3b | 90 | 17 | 4-OCH3 | 4-CH3 | 3ab | 93 |
3 | 4-CH3 | 4-Cl | 3c | 91 | 18 | 4-F | 4-CH3 | 3ac | 92 |
4 | 4-CH3 | 4-Br | 3d | 90 | 19 | 4-Cl | 4-CH3 | 3ad | 92 |
5 | 4-CH3 | 4-I | 3e | 89 | 20 | 4-Br | 4-CH3 | 3ae | 91 |
6 | 4-CH3 | 4-OCF3 | 3f | 90 | 21 | 4-OCF3 | 4-CH3 | 3af | 90 |
7 | 4-CH3 | 4-CN | 3g | 86 | 22 | 4-COOCH3 | 4-CH3 | 3ag | 88 |
8 | 4-CH3 | 2-OCH3 | 3h | 92 | 23 | 3-F | 4-CH3 | 3ah | 92 |
9 | 4-CH3 | 2-F | 3i | 88 | 24 | 3-Cl | 4-CH3 | 3ai | 91 |
10 | 4-CH3 | 2-Cl | 3j | 89 | 25 | 3-Br | 4-CH3 | 3aj | 92 |
11 | 4-CH3 | 2-Br | 3k | 90 | 26 | 3-NO2 | 4-CH3 | 3ak | 87 |
12 | 4-CH3 | 2,4-Cl2 | 3l | 90 | 27 | 2-CH3 | 4-CH3 | 3al | 90 |
13 | 4-CH3 | 2-Br-4-F | 3m | 87 | 28 | 2-F | 4-CH3 | 3am | 90 |
14 | 4-CH3 | 3-F-4-OCH3 | 3n | 91 | 29 | 2-Cl | 4-CH3 | 3an | 91 |
15 | | 3o | 88 | 30 | 2-Br | 4-CH3 | 3ao | 89 | |
31 | 2-CF3 | 4-CH3 | 3ap | 86 | |||||
32 | | 3aq | 87 |
Entry | R1 | R2 | 3 | Yield/% | Entry | R1 | R2 | 3 | Yield/% |
---|---|---|---|---|---|---|---|---|---|
1 | 4-CH3 | H | 3a | 95 | 16 | H | 4-CH3 | 3aa | 95 |
2 | 4-CH3 | 4-F | 3b | 90 | 17 | 4-OCH3 | 4-CH3 | 3ab | 93 |
3 | 4-CH3 | 4-Cl | 3c | 91 | 18 | 4-F | 4-CH3 | 3ac | 92 |
4 | 4-CH3 | 4-Br | 3d | 90 | 19 | 4-Cl | 4-CH3 | 3ad | 92 |
5 | 4-CH3 | 4-I | 3e | 89 | 20 | 4-Br | 4-CH3 | 3ae | 91 |
6 | 4-CH3 | 4-OCF3 | 3f | 90 | 21 | 4-OCF3 | 4-CH3 | 3af | 90 |
7 | 4-CH3 | 4-CN | 3g | 86 | 22 | 4-COOCH3 | 4-CH3 | 3ag | 88 |
8 | 4-CH3 | 2-OCH3 | 3h | 92 | 23 | 3-F | 4-CH3 | 3ah | 92 |
9 | 4-CH3 | 2-F | 3i | 88 | 24 | 3-Cl | 4-CH3 | 3ai | 91 |
10 | 4-CH3 | 2-Cl | 3j | 89 | 25 | 3-Br | 4-CH3 | 3aj | 92 |
11 | 4-CH3 | 2-Br | 3k | 90 | 26 | 3-NO2 | 4-CH3 | 3ak | 87 |
12 | 4-CH3 | 2,4-Cl2 | 3l | 90 | 27 | 2-CH3 | 4-CH3 | 3al | 90 |
13 | 4-CH3 | 2-Br-4-F | 3m | 87 | 28 | 2-F | 4-CH3 | 3am | 90 |
14 | 4-CH3 | 3-F-4-OCH3 | 3n | 91 | 29 | 2-Cl | 4-CH3 | 3an | 91 |
15 | | 3o | 88 | 30 | 2-Br | 4-CH3 | 3ao | 89 | |
31 | 2-CF3 | 4-CH3 | 3ap | 86 | |||||
32 | | 3aq | 87 |
Compd. | 50 μmol•L–1 | 25 μmol•L–1 | Compd. | 50 μmol•L–1 | 25 μmol•L–1 | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
发芽率/% | 抑制率/% | 发芽率/% | 抑制率/% | 发芽率/% | 抑制率/% | 发芽率/% | 抑制率/% | |||||
3a | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ac | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3b | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ad | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3c | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ae | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3d | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3af | 0.0±0.0 | 100.0±0.0 | 5.6±1.9 | 88.9±3.8 | |||
3e | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ag | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3f | 0.0±0.0 | 100.0±0.0 | 4.4±1.9 | 91.1±3.8 | 3ah | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3g | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ai | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3h | 0.0±0.0 | 100.0±0.0 | 12.2±3.8 | 75.6±7.7 | 3aj | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3i | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ak | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3j | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3al | 0.0±0.0 | 100.0±0.0 | 5.6±1.9 | 88.9±3.8 | |||
3k | 0.0±0.0 | 100.0±0.0 | 12.2±3.8 | 75.6±7.7 | 3am | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3l | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3an | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3m | 0.0±0.0 | 100.0±0.0 | 7.8±1.9 | 84.4±3.8 | 3ao | 0.0±0.0 | 100.0±0.0 | 8.9±1.9 | 82.2±3.8 | |||
3n | 0.0±0.0 | 100.0±0.0 | 5.6±1.9 | 88.9±3.8 | 3ap | 0.0±0.0 | 100.0±0.0 | 6.7±0.0 | 86.7±0.0 | |||
3o | 0.0±0.0 | 100.0±0.0 | 4.4±1.9 | 91.1±3.8 | 3aq | 0.0±0.0 | 100.0±0.0 | 6.7±0.0 | 86.7±0.0 | |||
3aa | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | ABA | 0.0±0.0 | 100.0±0.0 | 6.7±0.0 | 86.7±0.0 | |||
3ab | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | CK | 50.0±3.3 (0.5% DMSO) |
Compd. | 50 μmol•L–1 | 25 μmol•L–1 | Compd. | 50 μmol•L–1 | 25 μmol•L–1 | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
发芽率/% | 抑制率/% | 发芽率/% | 抑制率/% | 发芽率/% | 抑制率/% | 发芽率/% | 抑制率/% | |||||
3a | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ac | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3b | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ad | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3c | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ae | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3d | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3af | 0.0±0.0 | 100.0±0.0 | 5.6±1.9 | 88.9±3.8 | |||
3e | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ag | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3f | 0.0±0.0 | 100.0±0.0 | 4.4±1.9 | 91.1±3.8 | 3ah | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3g | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ai | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3h | 0.0±0.0 | 100.0±0.0 | 12.2±3.8 | 75.6±7.7 | 3aj | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3i | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3ak | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3j | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3al | 0.0±0.0 | 100.0±0.0 | 5.6±1.9 | 88.9±3.8 | |||
3k | 0.0±0.0 | 100.0±0.0 | 12.2±3.8 | 75.6±7.7 | 3am | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3l | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | 3an | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | |||
3m | 0.0±0.0 | 100.0±0.0 | 7.8±1.9 | 84.4±3.8 | 3ao | 0.0±0.0 | 100.0±0.0 | 8.9±1.9 | 82.2±3.8 | |||
3n | 0.0±0.0 | 100.0±0.0 | 5.6±1.9 | 88.9±3.8 | 3ap | 0.0±0.0 | 100.0±0.0 | 6.7±0.0 | 86.7±0.0 | |||
3o | 0.0±0.0 | 100.0±0.0 | 4.4±1.9 | 91.1±3.8 | 3aq | 0.0±0.0 | 100.0±0.0 | 6.7±0.0 | 86.7±0.0 | |||
3aa | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | ABA | 0.0±0.0 | 100.0±0.0 | 6.7±0.0 | 86.7±0.0 | |||
3ab | 0.0±0.0 | 100.0±0.0 | 0.0±0.0 | 100.0±0.0 | CK | 50.0±3.3 (0.5% DMSO) |
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